EP0043937B1 - Composés anthraquinone-azoiques, leur préparation et leur utilisation - Google Patents
Composés anthraquinone-azoiques, leur préparation et leur utilisation Download PDFInfo
- Publication number
- EP0043937B1 EP0043937B1 EP81104700A EP81104700A EP0043937B1 EP 0043937 B1 EP0043937 B1 EP 0043937B1 EP 81104700 A EP81104700 A EP 81104700A EP 81104700 A EP81104700 A EP 81104700A EP 0043937 B1 EP0043937 B1 EP 0043937B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- chlorine
- nitro
- alkoxy
- optionally substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 0 CNNC*(N)OC Chemical compound CNNC*(N)OC 0.000 description 3
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0018—Monoazo dyes prepared by diazotising and coupling from diazotized aminopolycyclic rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
- C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
- C09B29/3626—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B56/00—Azo dyes containing other chromophoric systems
- C09B56/12—Anthraquinone-azo dyes
Definitions
- the invention relates to anthraquinonazo compounds in one of their tautomeric structures of the formula correspond, processes for their preparation and their use as pigments.
- Azo pigments from pyridone coupling components have already been described in DE-OS 2 216 207. Surprisingly, it has now been found that the anthraquinonazo pigments of the formula (I) have excellent fastness properties, in particular light and weather fastness, and therefore represent an enrichment of the technology.
- Dyes from pyridone coupling components are also known from FR-A 2 381 807 and DE-A 1 932 809. However, these are disperse dyes, as the disclosed suitability for dyeing synthetic textile materials shows.
- the compounds according to the invention are pigments which are distinguished by their insolubility in the application medium. This property leads to the typical pigment properties such as fastness to solvents, fastness to overcoating, fastness to overspray and fastness to oils.
- Aminoanthraquinones of the formula are used to prepare the anthraquinone derivatives (I) in which A has the meaning given above, diazotized and with coupling components of the formula in which R 1 , R 2 and R 3 have the meaning given above, implemented.
- the anthraquinonazo compounds of the formula (I) can be prepared by a number of processes.
- a nitrocellulose varnish consisting of 44 g collodion wool (low viscosity, 35%, butanol-moist), 5 g dibutyl phthalate, 40 g ethyl acetate, 20 g toluene, 4 g n-butanol and 10 g glycol monomethyl ether are 6 g finely divided pigment according to the example 1a rubbed in. After spreading and drying, yellow coatings with excellent lightfastness and overcoating fastness are obtained.
- plasticizers e.g. B. can be understood: phthalic acid esters such as dioctyl phthalate, dibutyl phthalate, esters of phosphoric acid, castor oil alone or in combination with oil-modified alkyd resins.
- Coatings with similar fastness properties can be obtained using other physically drying spray, zapon and nitro paints, air-drying oil, synthetic resin and nitro combination paints, oven and air-drying epoxy resin paints, optionally in combination with urea, melamine, alkyd or phenolic resins .
- Example 1a 5 g of finely divided pigment according to Example 1a are ground in 100 g of a paraffin-free drying unsaturated polyester resin in a porcelain ball mill. With the grind 10 g of styrene. 59% melamine-formaldehyde resin and 1 g of a paste of 40 g cyclohexanone peroxide and 60 g dibutyl phthalate are mixed well and finally 4 g of drying solution (10% cobalt naphthenate in white spirit) and 1 g silicone oil solution (1% in xylene) are added. The mixture is applied to primed wood and a high-gloss, waterproof and weatherproof yellow coating is obtained with excellent lightfastness.
- Pigments of similar fastness are obtained when other two-component paints based on aromatic or aliphatic isocyanates and hydroxyl-containing polyethers or polyesters are used, and with moisture-drying polyisocyanate paints resulting in polyurea paints.
- a fine dough obtained by kneading 50 g of the pigment obtained according to Example 1a with 15 g of an arylpolyglycol ether emulsifier and 35 g of water are mixed with 10 g of heavy spar as a filler, 10 g of titanium dioxide (rutile type) as a white pigment and 40 g of an aqueous emulsion paint , containing approx. 50% polyvinyl acetate, mixed.
- the paint is spread and, after drying, yellow coatings are obtained with very good fastness to lime and cement as well as excellent weather and light fastness.
- the fine dough obtained by kneading is equally suitable for pigmenting clear polyvinyl acetate emulsion paints, for emulsion paints that contain copolymers of styrene and maleic acids as binders, and for emulsion paints based on polyvinyl propionate, polymethacrylate or butadiene styrene.
- a mixture of 65 g of polyvinyl chloride, 35 g of diisooctyl phthalate, 2 g of dibutyltin mercaptide, 0.5 g of titanium dioxide and 0.5 g of the pigment from example 1a is dyed on a mixing roller at 165 ° C.
- An intensely yellow-colored mass is obtained which can be used for the production of films or moldings.
- the coloring is characterized by excellent light and very good softening properties.
- 0.2 g of pigment according to Example 1a are mixed with 100 g of polyethylene, polypropylene or polystyrene granules.
- the mixture can either be sprayed directly in an injection molding machine at 220 ° C. to 280 ° C., or processed into colored bars in an extrusion press or colored skins on the mixing roller mill.
- the bars or skins are optionally granulated and sprayed in an injection molding machine.
- the yellow moldings have very good fastness to light and migration.
- synergistic polyamides from caprolactam or adipic acid and hexamethylenediamine or the condensates from terephthalic acid and ethylene glycol can be colored at 280-300 ° C., optionally under a nitrogen atmosphere.
- 1 g of pigment according to example 1a, 10 g of titanium dioxide (rutile type) and 100 g of a copolymer in powder form based on acrylonitrile-butadiene-styrene are mixed and dyed on a roller mill at 140-180 ° C.
- a yellow-yellow-colored fur is obtained, which is granulated and sprayed in an injection molding machine at 200-250 ° C. Yellow moldings with good light and migration fastness and good heat resistance are obtained.
- plastics based on cellulose acetate, cellulose butyrate and their mixture are colored with similar fastness properties.
- 0.2 g of pigment according to Example 1a are mixed in finely divided form with 100 g of a polycarbonate-based plastic in an extruder or in a kneading screw at 250-280 ° C. and processed into granules. A yellow, transparent granulate with excellent light fastness and heat resistance is obtained.
- 90 g of a weakly branched polyester of adipic acid, diethylene glycol and trimethylolpropane with a molecular weight of 2000 and a hydroxyl number of 60 are mixed with the following components: 1.2 g of dimethylbenzylamine, 2.5 g of sodium castor oil sulfate, 2.0 g of an oxyethylated, benzylated Oxidinphenyls, 1.75 g of water, 12 g of a paste, prepared by grinding 10 g of the pigment according to Example 1a in 50 g of the above-mentioned polyester.
- a printing paste is prepared from 10 g of the pigment fine dough specified in Example 57, 100 g of 3% tragacanth, 100 g of an aqueous 50% egg albumin solution and 25 g of a nonionic wetting agent.
- a textile fiber fabric is printed, steamed at 100 ° C. and a yellow print is obtained which is distinguished by excellent fastness properties, in particular light fastness properties.
- binders which can be used for fixing to the fiber, for example those based on synthetic resin, British gum or cellulose glycolate, can be used in the printing batch.
- a mixture of 100 g of light crepe, 2.6 g of sulfur, 1 g of stearic acid, 1 g of mercaptobenzothiazole, 0.2 g of hexamethylenetetramine, 5 g of zinc oxide, 60 g of chalk and 2 g of titanium dioxide (anatase type) is on a mixing mill at 50 ° C. and colored with 2 g of the pigment obtained according to Example 1 and then vulcanized for 12 minutes at 140 ° C. A yellow-colored vulcanizate with very good lightfastness is obtained.
- Example 1 a 100 g of a 20% aqueous paste of the pigment according to Example 1 a, for example, prepared by dissolving the dye in 96% sulfuric acid, removing it on ice, filtering and washing with neutral water, 22.5 l of an aqueous, approximately 9% viscose solution in Agitator added. The colored mass is stirred for 15 minutes, then deaerated and subjected to a spinning and desulfurization process. Yellow threads or foils with very good light fastness are obtained.
- the yellow pigmented paper produced according to Example 69 is soaked with the 55% solution of a urea-formaldehyde resin in n-butanol and baked at 140 ° C. A yellow laminate paper with very good migration and excellent light fastness is obtained.
- Laminate paper of the same fastness is obtained by laminating a paper which has been gravure-printed with a printing ink which contains the yellow pigment paste shown in Example 57 and water-soluble or saponifiable binders.
- 20 g of the pigment obtained according to Example 1a are finely dispersed in a bead mill in 50 g of dimethylformamide using a dispersing aid consisting of 50 g of a 10% strength solution of polyacrylonitrile in dimethylformamide.
- the pigment concentrate thus obtained is added to the spinning solution of polyacrylonitrile in a known manner, homogenized and then spun into filaments by known dry or wet spinning processes.
- Yellow colored filaments are obtained, the coloring of which is distinguished by very good fastness to rubbing, washing, migration, heat, light and weather.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paints Or Removers (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (10)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19803024857 DE3024857A1 (de) | 1980-07-01 | 1980-07-01 | Anthrachinonazo-verbindungen, verfahren zu ihrer herstellung sowie ihre verwendung |
DE3024857 | 1980-07-01 |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0043937A2 EP0043937A2 (fr) | 1982-01-20 |
EP0043937A3 EP0043937A3 (en) | 1982-01-27 |
EP0043937B1 true EP0043937B1 (fr) | 1984-09-19 |
Family
ID=6106114
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP81104700A Expired EP0043937B1 (fr) | 1980-07-01 | 1981-06-19 | Composés anthraquinone-azoiques, leur préparation et leur utilisation |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP0043937B1 (fr) |
JP (1) | JPS5774362A (fr) |
DE (2) | DE3024857A1 (fr) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2368443T3 (es) * | 2005-05-13 | 2011-11-17 | Huntsman Advanced Materials (Switzerland) Gmbh | Mezclas de tinción. |
TR201907659T4 (tr) * | 2012-06-06 | 2019-06-21 | Huntsman Adv Mat Switzerland | Antrakinon azo boyaları. |
JP6165253B2 (ja) | 2012-09-12 | 2017-07-19 | ハンツマン アドバンスト マテリアルズ (スイッツァランド) ゲーエムベーハーHuntsman Advanced Materials (Switzerland) Gmbh | インク及び織物繊維材料をインクジェット印刷する方法 |
WO2018114140A1 (fr) | 2016-12-20 | 2018-06-28 | Huntsman Advanced Materials (Switzerland) Gmbh | Encres et procédé d'impression par jet d'encre de matériaux de fibres textiles |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1249641A (en) * | 1968-06-27 | 1971-10-13 | Ici Ltd | Coloration process |
GB1256093A (en) * | 1968-06-27 | 1971-12-08 | Ici Ltd | Water-insoluble monoazo dyestuffs |
DE2708418A1 (de) * | 1977-02-26 | 1978-08-31 | Cassella Farbwerke Mainkur Ag | Wasserunloesliche azofarbstoffe und verfahren zu ihrer herstellung, sowie deren kupplungskomponenten und verfahren zur herstellung der kupplungskomponenten |
DE2930481A1 (de) * | 1979-07-27 | 1981-02-12 | Bayer Ag | Anthrachinonazo-verbindungen, verfahren zu ihrer herstellung sowie ihre verwendung als pigmente |
-
1980
- 1980-07-01 DE DE19803024857 patent/DE3024857A1/de not_active Withdrawn
-
1981
- 1981-06-19 DE DE8181104700T patent/DE3166164D1/de not_active Expired
- 1981-06-19 EP EP81104700A patent/EP0043937B1/fr not_active Expired
- 1981-06-26 JP JP56098461A patent/JPS5774362A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
DE3166164D1 (en) | 1984-10-25 |
JPS5774362A (en) | 1982-05-10 |
EP0043937A3 (en) | 1982-01-27 |
DE3024857A1 (de) | 1982-02-04 |
EP0043937A2 (fr) | 1982-01-20 |
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